A failed orginization or group of idiots. Doomed to failure and full of ineptitude, they still contiune to sail away on the sea of stupidity.
In extreme circumstances, one man can be catergorized as a failboat in and of his/her self.
Pictures of capsized or rolled boats usually shown as an example of what happens when the crew does something.

Hi! Im Al Gore and I invented the internet. Today I will be your captain of the SS Failboat.